(Z,Z)-11,14-Eicosadienoic acid (CHEM028345)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-26 00:23:32 UTC
Update Date2016-11-09 01:18:40 UTC
Accession NumberCHEM028345
Identification
Common Name(Z,Z)-11,14-Eicosadienoic acid
ClassSmall Molecule
DescriptionAn icosadienoic acid with double bonds at positions 11 and 14 (both Z).
Contaminant Sources
  • FooDB Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(11Z,14Z)-Eicosa-11,14-dienoic acidChEBI
(11Z,14Z)-Eicosadienoic acidChEBI
(11Z,14Z)-Icosa-11,14-dienoic acidChEBI
11,14-Eicosadienoic acidChEBI
11,14-Icosadienoic acidChEBI
(11Z,14Z)-Eicosa-11,14-dienoateGenerator
(11Z,14Z)-EicosadienoateGenerator
(11Z,14Z)-Icosa-11,14-dienoateGenerator
11,14-EicosadienoateGenerator
11,14-IcosadienoateGenerator
EicosadienoateGenerator
11, 14-IcosadienoateHMDB
11, 14-Icosadienoic acidHMDB
11,14-trans-Eicosadienoic acidHMDB
delta11,14-20:2HMDB
Eicosa-11,14-dienoic acidHMDB
Eicosa-11,14-dienoic acid, (Z,Z)-isomerHMDB
N-6 Eicosadienoic acidHMDB
DihomolinoleateHMDB
(11Z,14Z)-IcosadienoateHMDB
(11Z,14Z)-11,14-EicosadienateHMDB
(11Z,14Z)-11,14-Eicosadienic acidHMDB
(11Z,14Z)-11,14-EicosadienoateHMDB
(11Z,14Z)-11,14-Eicosadienoic acidHMDB
11,14-all-cis-EicosadienoateHMDB
11,14-all-cis-Eicosadienoic acidHMDB
11-cis,14-cis-EicosadienoateHMDB
11-cis,14-cis-Eicosadienoic acidHMDB
BishomolinoleateHMDB
Bishomolinoleic acidHMDB
Dihomo-linoleate (20:2n6)HMDB
Dihomo-linoleic acid (20:2n6)HMDB
FA(20:2(11Z,14Z))HMDB
Homo-gamma-linoleateHMDB
Homo-gamma-linoleic acidHMDB
Homo-γ-linoleateHMDB
Homo-γ-linoleic acidHMDB
all-cis-11,14-EicosadienoateHMDB
all-cis-11,14-Eicosadienoic acidHMDB
cis,cis-Eicosa-11,14-dienoateHMDB
cis,cis-Eicosa-11,14-dienoic acidHMDB
cis,cis-delta11,14-EicosadienoateHMDB
cis,cis-delta11,14-Eicosadienoic acidHMDB
cis,cis-Δ11,14-eicosadienoateHMDB
cis,cis-Δ11,14-eicosadienoic acidHMDB
cis-11,cis-14-EicosadienoateHMDB
cis-11,cis-14-Eicosadienoic acidHMDB
delta11,14-EicosadienoateHMDB
delta11,14-Eicosadienoic acidHMDB
Δ11,14-eicosadienoateHMDB
Δ11,14-eicosadienoic acidHMDB
FA(20:2n6)HMDB
Eicosadienoic acidChEBI
Chemical FormulaC20H36O2
Average Molecular Mass308.499 g/mol
Monoisotopic Mass308.272 g/mol
CAS Registry Number5598-38-9
IUPAC Name(11Z,14Z)-icosa-11,14-dienoic acid
Traditional Nameeicosadienoic acid
SMILESCCCCC\C=C\C\C=C\CCCCCCCCCC(O)=O
InChI IdentifierInChI=1S/C20H36O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10H,2-5,8,11-19H2,1H3,(H,21,22)/b7-6+,10-9+
InChI KeyXSXIVVZCUAHUJO-AVQMFFATSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentLong-chain fatty acids
Alternative Parents
Substituents
  • Long-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility5.4e-05 g/LALOGPS
logP7.83ALOGPS
logP7.31ChemAxon
logS-6.8ALOGPS
pKa (Strongest Acidic)4.95ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count16ChemAxon
Refractivity97.72 m³·mol⁻¹ChemAxon
Polarizability39.94 ųChemAxon
Number of Rings0ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9760000000-cd3039251f27ed659833Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9652000000-051c308924d68202698fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , negativesplash10-000i-0091000000-cd5567f72a97a19a5daaSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-0006-0290000000-26edae55398bbe6d8f14Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 30V, positivesplash10-003v-9200000000-f117dd4d613f97c9e9a1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 33V, positivesplash10-003u-9100000000-64feb0d0359edf0e55faSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 37V, positivesplash10-003u-9100000000-1c5be01a286361015756Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 40V, positivesplash10-005c-9100000000-2af5db21026406ee4f51Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 44V, positivesplash10-005c-9100000000-900bb2bb1942a2772e06Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-05o0-1900000000-87b112cb6d02616a7390Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0a4i-0009000000-66380db5e2f48c28d914Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0a4i-0009000000-37933ac7549ff468e6e0Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0a4i-0019000000-139b1c14ace122806206Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0a4i-0049000000-bea23a8f63f68b2a2579Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-052g-3594000000-9f6dd586ee4aa178e78eSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-0hka-0930000000-500174f550638fdb0b03Spectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-00di-0490000000-80d1e0e8b9b35e163450Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0006-0090000000-cf7b1131f470250aedcbSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0006-0090000000-32033519d24a370bbb6eSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 10V, positivesplash10-0006-2590000000-f57018cf6f280ddd27bdSpectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 14V, positivesplash10-059w-7930000000-7f2165e3d0add956aa59Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 17V, positivesplash10-053s-9600000000-4f5ff0e39e1f3cb65e88Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 22V, positivesplash10-053s-9300000000-8f9cd251a7bb707f1544Spectrum
LC-MS/MSLC-MS/MS Spectrum - Orbitrap 28V, positivesplash10-001m-9100000000-176d923c10fc2cf41b6cSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-00di-1890000000-ea581730d6da2112857dSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-014i-9000000000-1170a17e0bd60829ce3fSpectrum
LC-MS/MSLC-MS/MS Spectrum - n/a 21V, positivesplash10-001i-9000000000-3e1931835afb9d465af4Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDNot Available
HMDB IDHMDB0005060
FooDB IDFDB012619
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkNot Available
Chemspider ID4944228
ChEBI ID73731
PubChem Compound ID6439848
Kegg Compound IDC16525
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. Jensen RG, Ferris AM, Lammi-Keefe CJ: The composition of milk fat. J Dairy Sci. 1991 Sep;74(9):3228-43. doi: 10.3168/jds.S0022-0302(91)78509-3.
2. Glasser F, Ferlay A, Chilliard Y: Oilseed lipid supplements and fatty acid composition of cow milk: a meta-analysis. J Dairy Sci. 2008 Dec;91(12):4687-703. doi: 10.3168/jds.2008-0987.
3. Kurt J. Boudonck, Matthew W. Mitchell, Jacob Wulff and John A. Ryals. Characterization of the biochemical variability of bovine milk using metabolomics. Metabolomics (2009) 5:375?386
4. M. Ferrand et al. Determination of fatty acid profile in cow's milk using mid-infrared spectrometry: Interest of applying a variable selection by genetic algorithms before a PLS regression. Chemometrics and Intelligent Laboratory Systems 106 (2011) 183?189
5. Minda H, Kovacs A, Funke S, Szasz M, Burus I, Molnar S, Marosvolgyi T, Decsi T: Changes of fatty acid composition of human milk during the first month of lactation: a day-to-day approach in the first week. Ann Nutr Metab. 2004;48(3):202-9. Epub 2004 Jul 13.
6. Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043.
7. Lipid Maps (LMFA01030130): http://www.lipidmaps.org/data/LMSDRecord.php?LMID=LMFA01030130